Acetone → HCID 86627656, compound

HRID 1907950Notes

Reaction equation

HRID 1907950 reaction equation
NN.O=C1C2C(=CC=CC=2)C(=O)[N:5]1[O:14][CH2:15][C:16]1[N:17]([CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:39])[CH:36]([CH3:38])[CH3:37])[C:18]2[C:23]([CH3:24])=[C:22]([CH3:25])[N:21]3[N:26]=[N:27][N:28]=[C:20]3[C:19]=2[N:29]=1.ClCCl.[CH3:43][C:44]([CH3:46])=O>C(O)C>[CH3:25][C:22]1[N:21]2[N:26]=[N:27][N:28]=[C:20]2[C:19]2[N:29]=[C:16]([CH2:15][O:14][N:5]=[C:44]([CH3:46])[CH3:43])[N:17]([CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:39])[CH:36]([CH3:37])[CH3:38])[C:18]=2[C:23]=1[CH3:24]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 9321HydrazineHCID 67052268HCID 67052268, compound

Product 1

HCID 86627656HCID 86627656, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous hydrazine (0.91 mL, 29 mmol) was added to a stirred suspension of N-[4-(8-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butyl]-2-methylpropanamide (4.90 g, 9.71 mmol) in ethanol (100 mL). Dichloromethane (50 mL) was added. After four hours, acetone (50 mL) was added and the reaction mixture was stirred overnight. A solid was removed by filtration and washed with methanol. The filtrate was concentrated to provide a solid that was triturated with 1:1 saturated aqueous sodium bicarbonate/water. The solid was isolated by filtration, washed with water, and dissolved in chloroform (300 mL). The solution was washed with water (2×50 mL), dried over sodium sulfate, filtered, concentrated under reduced pressure, and dried under vacuum to afford N-{4-[5,6-dimethyl-8-({[(1-methylethylidene)amino]oxy}methyl)-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butyl}-2-methylpropanamide that was used in the next experiment.

Workup

  1. customA solid was removed by filtration
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated
  4. customto provide a solid
  5. customthat was triturated with 1:1 saturated aqueous sodium bicarbonate/water
  6. customThe solid was isolated by filtration
  7. washwashed with water
  8. dissolutiondissolved in chloroform (300 mL)
  9. washThe solution was washed with water (2×50 mL)
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customdried under vacuum

Sources & evidence

ORD record
ord-434ad99184494779b1bbf459eb9f5f68
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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